Honeywell International Inc.

Rajesh K Dubey

Sudip Mukhopadhyay

Hsueh Sung Tung

Michael Van Der Puy

Daniel C Merkel

Haridasan K Nair

Jing Ji Ma

Steven D Phillips

Cheryl L Bortz

Barbara A Light

Rajiv R Singh

Kim M Fleming

George A Shia

Haiyou Wang

Robert C Johnson

Richard Udy

Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CFCF&#x2550;CH(1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl&#x2550;CClCHCl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CFCCl&#x2550;CH, preferably in a 80-96% selectivity. The CFCCl&#x2550;CHis preferably converted to CFCFClCH(244-isomer) using a SbClas the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of CrOand FeCl/C is preferably used as the catalyst to achieve high selectivity to CFCCl&#x2550;CH(96%). In the second step, SbCl/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CFCFClCH. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.

Method for producing fluorinated organic compounds

Disclosed is a method for producing fluorinated organic compounds, including reacting CF&#x2550;CFCl with CHFCl under conditions effective to produce a product composition including CFCClFCHCl. The present invention also relates to the production of hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I):CFCFCHX&#x2003;&#x2003;(I)to at least one compound of formula (II)CFCZCHZ&#x2003;&#x2003;(II).where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a&#x2212;m&#x2267;0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).

A method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I):CF(&#x2014;CXX)CX&#x2550;H&#x2003;&#x2003;(I)to at least one compound of formula (II):CF(CXX)CX&#x2550;H&#x2003;&#x2003;(II),where Xis Cl, Br or I, each Xis independently selected from the group consisting of H, Cl, F, Br or J, and n is 0, 1, or 2.

Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CFCF&#x2550;CH(1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl&#x2550;CClCHCl is fluorinated to synthesize a compound such as CFCCl&#x2550;CH. The CFCCl&#x2550;CHis preferably converted to CFCFClCH(244-isomer) using a SbClas the catalyst which is then transformed selectively to 1234yf. For the first step, a mixture of CrOand FeCl/C is preferably used as the catalyst to achieve high selectivity to CFCCl&#x2550;CH(96%). In the second step, SbCl/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CFCFClCH. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.

Disclosed are methods for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I):CFCHXCHX&#x2003;&#x2003;(I)to at least one compound of formula (II)CFCZCHZ&#x2003;&#x2003;(II).where X is independently Cl, Br, I or F, and Z independently is H or F. In certain preferred embodiments, each Z is different.

Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I):CFCFCHX&#x2003;&#x2003;(I)to at least one compound of formula (II)CFCZCHZ&#x2003;&#x2003;(II).where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a-m&#x2267;0. Certain embodiments include the step of reacting fluorinated Colefin, such as tetrafluoroethylene, with a Cl addition agent under conditions effective to produce a compound of formula (I).

A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.

Gas phase synthesis of 2,3,3,3-tetrafluoro-1-propene from 2-chloro-3,3,3-trifluoro-1-propene

Disclosed is a method for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I):CFCFCHX&#x2003;&#x2003;(I)to at least one compound of formula (II)CFCZCHZ&#x2003;&#x2003;(II).

A method for preparing fluorinated organic compounds comprising contacting hydrogen fluoride with at least one compound of formula I:CXCXYCH&#x2003;&#x2003;Iwhere each X is independently Cl, I or Br, and each Y is independently H or F, said contacting step being carried out under conditions effective to produce a compound of formula IICFCZCH&#x2003;&#x2003;IIwhere Z is Cl, I, Br, or F.

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Williamsville, NY, United States of America

Rajesh K Dubey